HCID 15200286, compound → HCID 131717350, compound

HRID 1195657Notes

Reaction equation

C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([C@@H:23]2[CH2:25][C@H:24]2[C:26]([NH:28][CH3:29])=[O:27])[CH2:6]1)(=O)C.O(P(O[C:47]1[C@H:48]([CH3:71])[C@H:49]2[C@@H:66]([C@H:67]([OH:69])[CH3:68])[C:65](=[O:70])[N:50]2[C:51]=1[C:52]([O:54][CH2:55]C1C=CC([N+]([O-])=O)=CC=1)=[O:53])(OC1C=CC=CC=1)=O)C1C=CC=CC=1>>[OH:69][C@@H:67]([C@H:66]1[C:65](=[O:70])[N:50]2[C:51]([C:52]([O:54][CH2:55][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[O:53])=[C:47]([S:4][C@@H:5]3[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]4[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=4)=[O:11])[C@H:7]([C@@H:23]4[CH2:25][C@H:24]4[C:26]([NH:28][CH3:29])=[O:27])[CH2:6]3)[C@H:48]([CH3:71])[C@H:49]12)[CH3:68]

Participants

Reactant 2

HCID 15200286HCID 15200286, compound

HCID 57121762HCID 57121762, compound

Product 1

HCID 131717350HCID 131717350, compoundYield 223.7%

Procedure

The same procedure as in EXAMPLE 1a and 1b was carried out by using trans-2-[(2S,4S)-4-acetylthio-N-(4-nitrobenzyloxycarbonyl) pyrrolidin-2-yl]-N-methylcyclopropanecarboxamide (180 mg, 0.42 mmol)and 4-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate(203 mg, 0.34 mmol) to give 4-nitrobenzyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-[trans-2-(N-methylaminocarbonyl) cyclopropyl]-N-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (340 mg).

Sources & evidence

ORD record: ord-c10a732a413e4a359830a58f9f15dbd2
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05112818

Reaction notes

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